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Paper | Regular issue | Vol 38, No. 11, 1994, pp.2389-2399
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6791
Halogenated Isoniazid Derivatives. Part 2. Unusual Synthesis of Δ2-1,3,4-Oxadiazoline Derivatives from Isonicotinoylhydrazones and Diazomethane

Rosaria Ottana, Enrico Rotondo, M. Gabriella Vigorita,* Carmela Zappala, and Gluseppe Giordano

*Dipartimento Farmaco-Chimico, Università di Messina, Viale Annunziata, 98168 Messina, Italy

Abstract

The synthesis of a representative group of isoniazid derivatives, namely 5-aryl-4-methyl-2-pryidyl-Δ2-1,3,4-oxadiazolines (3) and 4-aryl-1-methoxy-1-pyridyl-2,3-diazabutandienes (2) by reaction of isonicotinoylhydrazones (1) with diazomethane is described. A mechanism for the unexpected formation of 3 is suggested.